As Dusk Falls

When you get to the party with Vanessa decline drugs, wait in hallway, walk away from them, say you are jealous, don’t hit him again leave him. After the party jay and Vanessa will go to the cliff. Tell her that you lied to her, she will eventually kiss you. Kiss her back. Not sure if these matter or not but I thought I would add a more detailed guide as there are TWO MAJOR choices through these scenes worth noting this is exactly what I did to obtain achievement.

Chapter 5 at the party: Don't fight Todd and at campground kiss Vanessa back.

For a Full and Fast Achievements Guide check the link below:


Timestamps:

00:00 Intro + Useful Information
02:02 Chapter 1: Story
03:49 Chapter 1: Code Breaker + Smooth Criminal Achievements
05:14 Chapter 1: Message Received + Tables Turned + And So It Begins… Achievements
06:32 Chapter 1: Bungled Achievement
07:16 Chapter 1: Cop Out + Point Blank Achievements
08:18 Chapter 2: What’s Your Emergency? Achievement
09:12 Chapter 2: Story
10:08 Chapter 2: Paging Dr. Walker Achievement
10:57 Chapter 2: Keeping The Faith + Second Chance + Lifesaver Achievements
11:56 Chapter 2: Dodged A Bullet + Caught in a Trap Achievements
12:21 Chapter 2: What’s Done is Done + Unforgiveable Achievements
13:32 Chapter 3: Long Arm of the Law
14:01 Chapter 3: Story
14:24 Chapter 3: Resurrection Achievement
14:48 Chapter 3: Take Me Instead + New Dawn + From Dusk ‘til Dawn Achievements
15:59 Chapter 3: Better the Devil You Know Achievement
16:23 Chapter 3: Buried Alive Achievement
16:44 Chapter 3: She’s Coming with Us Achievement
17:18 Chapter 4: Invincible Achievement
17:49 Chapter 4: Story
18:46 Chapter 4: Cabin? What Cabin? + Brothers in Arms + Into The Woods Achievements
19:46 Chapter 4: Trail of Breadcrumbs + Once a Holt + Hands in the Air + No Going Back Achievement
21:19 Chapter 5: Bullseye Achievement
22:04 Chapter 5: Plead the 5th Achievement
22:28 Chapter 5: Story
22:54 Chapter 5: Jailbird Achievement
23:23 Chapter 5: Heart to Heart + Bonnie and Clyde + Runaways Achievements
24:14 Chapter 5: Cuba Libre Achievement
24:58 Chapter 6: Story (Wait for the Cop)
25:43 Chapter 6: Into the Wild + Breaking Bread + Past, Tense + End of the Road? Achievements
26:56 Chapter 6: Almost Made It + Enough is Enough + Stay of Execution
27:47 Chapter 6: You’re On Your Own (Chapter5) + Free Bird + Most Wanted Achievements

Jay and Vanessa will arrive at Todd’s party in Chapter 5 and after finding Todd with Vanessa, you must choose Walk Away from Todd.

Jay will wait by the car and Vanessa will later leave the party.

Later Jay and Vanessa will be alone outside and she will eventually kiss Jay and I kissed Vanessa back and said I wanted her to come with me and then at the next save point the achievement unlocked.